A Founder’s Journey Includes Being Social Steve Weinberger

A Founder’s Journey Includes Being Social Steve Weinberger

VENTEUR spoke with Steve Weinberger, Senior Managing Director at HCR Wealth Advisors, about his entrepreneurial journey. Weinberger started at HCR Wealth Advisors in 1998 and has 20 years of experience in the financial services industry. He helps clients develop personalized investment portfolio strategies and points out exposure and potential risks to ensure that clients are ready for unexpected curve balls. He specializes in working with clients going through life transitions (E.g., retirement, widowhood, selling a business).

Before joining HCR Wealth Advisors, Weinberger worked at Prudential Insurance. He has an MBA with an emphasis in finance from Pepperdine’s Graziadio School of Business and Management.

Senior Managing Director at HCR Wealth Advisors Steve Weinberger / Photo courtesy of Steve Weinberger

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

The biggest lesson I have learned about myself is that I can accomplish whatever I set my mind to accomplish. 

Being an entrepreneur requires more dedication and perseverance than you may think, and there were times when I was unsure whether I had any more to give. But time after time, I could dig deep to find more and keep driving forward. 

Throughout my journey, there have been times of sacrifice and abundance, but regardless of the season, the constant has always been “go.” 

I always considered myself a determined person but being an entrepreneur has unlocked a level of determination that I was not even aware I had until I had no other choice.

I have also learned that proper balance is the key to success. 

This can be applied to your personal or professional life. 

Still, I have found that the most successful place to apply this philosophy is the intersection between my personal and professional lives. 

Once I could crack my unique code of balancing my personal and professional lives, I was happier, more productive, and less stressed.

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur? 

I did not experience loneliness because I was lucky to have a good business partner. We shared the weight of the responsibility of owning a business and bounced ideas off each other constantly. We have complementary skill sets, allowing both of us to take ownership of our specialties and grow as individual professionals while growing the business.

Although we always had each other, I wish we would have had more of a guided path to follow, especially during the early years. 

Registered Investment Advisory (RIA) firms were much fewer and far between than they are today when we got started, so although we knew we were on the right path (giving clients independent financial advice), we hadn’t seen what the path would or should look like, so many of our decisions had to be guided by pure instinct. 

We did not always know what would come next or where we would end up, which is an issue many entrepreneurs face, but it’s important to have the confidence to take steps forward.

The Psychological Warfare 

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur?

I did not experience those issues in particular, and I credit that to my approach to work. 

Early on in my life, I learned the value of having a good work-life balance, and I have always stayed true to that principle in my professional life. 

This balance gave me an advantage as an entrepreneur because it allowed me to operate optimally and fire on all cylinders, keeping me going. 

Eating healthy, sleeping, and exercising have always been core because I understood that when those elements align, I would be happier and more productive, which is good for the company and me.

My social life suffered a bit during the early years, but I could get that back on track once I started to pair social time with work or exercise. This also helped prevent me from experiencing isolation and loneliness.

Newer entrepreneurs often equate their personal success with the success and value of their business. If their business fails, they are a failure. If their business succeeds, they are a success. Have you experienced this warped perception of reality?

I have experienced that sense of reality. 

From a bird’s eye view, it makes logical sense to separate your personal feelings from the company’s successes or failures. Still, when you are in a business for over 20 years, and it becomes an extension of yourself, it is pretty difficult not to internalize things. 

I’ve always been goal-oriented and felt good when I accomplished goals, so it was only natural that, as a business owner, I did not feel good when we missed our goals. I try to be conscious of it, but it still creeps up every now and then. 

The real advantage comes when you can use your company’s successes or failures to fuel you in a productive way rather than allowing them to get you down.

When we didn’t close a client in the early days, it didn’t feel great. I would spend lots of time going over every interaction, trying to analyze why we weren’t successful at closing. It felt natural to get caught up in what could have been, but, eventually, I took that energy and turned it into fuel to hone my skills and gain more knowledge about the industry. This helped me develop as a professional and improve my closing rate.

I was always driven to succeed. 

One definition of success for me was tied to making money, but not in the traditional sense that more is better. 

I recognized that money was a means to achieve something much more important to me – having a lifestyle free from the worries and stresses that a lack of money can cause. 

I didn’t want to be prevented from making certain moves or decisions because a lack of money was stopping me. 

I wanted to be independent, and I eventually achieved that through finding financial freedom.

What are your three biggest fears as an entrepreneur, and how do you manage those fears?

1. Fear of Failure

I manage this by trying my best to work smart and have a clear plan and a vision that I remain true to. Over the years, I have learned that balancing short-term needs while keeping long-term goals in sight is crucial to success. I try not to get too caught up in the minutia and lose sight of the bigger picture. 

2. Fear of Not Being Respected by Peers in the Industry

This is something I battled with in the early years. To manage this, I tried to speed up my learning curve by reading and attending events to understand my industry better. Essentially, I tried to gain knowledge in any way that I could. I also spent a lot of time practicing until things felt more natural, which eased this fear tremendously.

3. Fear of Change

After years of battling this fear, I finally decided to embrace change. Change is all around us, and to keep up, you must be willing to leap with faith. You can’t wait until the moment feels 100% right because it will never come. Those who wait for it get left behind.

The Mistakes

What are three mistakes you made early on as an entrepreneur, what did you learn from them, and how can others avoid these mistakes?

1. I Used To Be Too Controlling

I wasn’t correctly utilizing the team around me; instead, I tried to do everything myself. Eventually, I couldn’t do everything, so I had to start delegating tasks and letting some things go to keep growing. To avoid this common entrepreneurial pitfall, I suggest figuring out your strengths and developing a team around you with complementary skills. Once you have the right team in place, you need to put them in positions to be successful and give them the autonomy and resources needed to accomplish their goals. I’ve had years of experience proving the adage: together, we go far.

2. I Used To Wait Too Long Before Making Decisions

In the early days, I was comfortable with the status quo and feared the unknown, so I didn’t see a need to rock the boat. But as the business grew, it needed to evolve, and so did I. Entrepreneurs need to recognize this complacency and take action before getting stuck on a plateau. 

Look for opportunities to upgrade your infrastructure, technology, and team whenever possible because these investments in your business will pay dividends. I was too slow to embrace this truly but I have tried to be more conscious of it in recent years.

3. I Didn’t Take Full Advantage of the Resources Around Me

In the early years especially, I was so engrossed in developing myself via reading and doing that I missed out on learning from colleagues and other people in my industry. I thought that my partner and I had to walk the path alone and didn’t take the time to recognize some available resources, including industry benchmarking data. We have now embraced our resources and used the lessons learned to continue to scale and grow.

What are three things you see that are often overlooked by entrepreneurs you encounter, and how can other entrepreneurs be aware of these things from the beginning?

1. The Importance of Having a Business Plan

Entrepreneurs frequently get bogged down every day and don’t take enough time to work on higher-level strategic initiatives. It is imperative to remove yourself as needed to work on the business rather than just in the business. To set yourself up for success, I encourage entrepreneurs to consider off-site strategy meetings with their executive team. These sessions have proven incredibly useful to me over the years and have helped ensure we’re all rowing in the same direction.

2. The Importance of Building Your Team

As an entrepreneur, you have to fight your instincts to do it all yourself. Having the right team will exponentially increase your success because it will allow you to rely on others’ strengths and focus on your strength. I recommend doing this sooner rather than later, even before you reach your max capacity. Once you reach that level, it will be challenging to allocate the time necessary to put the right team members in place.

3. The Importance of a Strong Culture

As an entrepreneur, you must consider what type of environment you want to create and recognize that the example for the entire team will come from the top, so you must walk the walk (and not just talk the talk). In this day and age, work culture has a resounding effect on the longevity of your staff. Employees want more than just a paycheck from their work; they crave a sense of belonging to a place that aligns with their values.

The Successes

What are three seemingly insurmountable obstacles you’ve faced as an entrepreneur, and how have you overcome them?

1. Cash Flow Management

In the private wealth management business, the way we presented ourselves was important. We needed to have a nice office and a fair amount of employees to execute all of the services that we provided to clients. We had to take on this overhead early on, regardless of what our revenue or profit looked like at the time. Meeting client expectations was key to our early success, so we had to make whatever sacrifices were necessary to do it.

2. Entering the Business at a Young Age

When I started this business, I was in my late 20s, which may not seem too young until you consider the average age of our clients was 65 and older. I struggled to figure out how to get them to trust me, considering the wide gap in our ages and life experiences. There were some bumps along the way, but I soon realized that the better I was at my job, the less my age mattered. So, I focused my time on professional development any chance I had.

3. Lack of Experience

I was afraid to admit when I didn’t know something during my early years. I thought I had to know everything, and I wasn’t comfortable sharing that I didn’t know something with colleagues or clients. As I matured as a person and professional, I realized that admitting when I didn’t know something wasn’t anything to be ashamed of, and I instead used that time to tap into my resources to find the answer. It takes confidence to be completely truthful in these types of situations, and it’s something I wish I had learned earlier on.

What are three ways you have managed to boost your productivity without causing burnout?

1. Investing in Building the Right Team

Looking back, I wish I would have realized this sooner. Having the right people in place gives me peace of mind that things are being well taken care of, which allows me to focus all of my energy on what I need to do to keep driving us forward.

2. Creating a Healthy and Fun Environment and Work Culture

We spend almost half of our waking lives at work, so why not make it somewhere you want to spend time? If the work is getting done, there is no reason not to take time to socialize, share a laugh, take a walk outside, or do whatever you need to rejuvenate. Our team is incredibly close, which has helped us weather the storms we’ve faced thus far.

3. Embracing Technology

We’re focusing on working smarter, not harder, and leveraging technology to enhance our output. It requires an investment but giving your team the tools to enhance their performance will only improve things in the long run.

The Advice

How can newer entrepreneurs develop a healthy work-life balance even when it seems like an impossible task?

Strategic calendaring techniques have helped our team be more productive and maintain a good work-life balance. There are several variations, but figuring out what you need to help balance out work (E.g., exercise, sleep, meal breaks, meditation, reading time, walks) and setting aside time for that on your calendar in advance, then scheduling calls, meetings, and other things around it, has been a game-changer. 

Some of our team members take it a step further and organize their workdays based on the types of activities. For example, they may reserve Tuesdays and Thursdays for external meetings, Mondays for deep (individual) work, Wednesdays for internal meetings, and Fridays for shallow (individual) work.

Personally, blending social activities into work or exercise whenever possible has helped me keep things balanced. When I tried to keep everything separated, I felt like I didn’t have enough time in the day for everything, but once I figured out how to strike the balance of blending activities, things became much more manageable.

What three key pieces of advice would have made your entrepreneurial journey easier, and why?

1. Embracing Technology

You can’t control everything. To be successful, you’ll have to rely on others so you might as well get started with that sooner rather than later.

2. Have a Clear Vision and Stay True to It

Things will never go 100% to plan, but as the landscape changes, your vision will be your guide through the new terrain. As best you can, try to remember to enjoy the journey, not just the destination.

3. Embracing Change

The industry and external environment will continuously change, and you have to accept that change because there will be no growth without it.

What do you think the most significant difference is between how an entrepreneur sees their career path versus how an employee at a company sees their career path, and why?

Entrepreneurs see their companies as something they have built. Their company feels like their baby, so, naturally, they are very attached to it. Because of this, entrepreneurs will always be more dedicated to the company and willing to do whatever it takes to succeed.

Employees don’t necessarily have the same dedication or attachment to a company. Some view their job as a stepping stone to get to the next level, which may not be within the same company. 

What role has intuition played in your success as an entrepreneur, and why do you think this is the case?

Intuition is key. As an entrepreneur, you’re constantly taking leaps of faith and often have to pave your way. Your intuition guides you, especially when going down an unpaved road. I have a good balance of intuition and practical intelligence, which has helped inform my decisions along the way.

Topic Contributors

Questions based in part on topics and comments provided by:

  1. Alicia Nagel, Founder at Alicia Nagel Creative
  2. Rob Volpe, Chief Executive Officer at Ignite 360
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